CA2482896A1 - Procede de production de poly-alpha-olefines a haute viscosite en utilisant des catalyseurs liquides ioniques - Google Patents
Procede de production de poly-alpha-olefines a haute viscosite en utilisant des catalyseurs liquides ioniques Download PDFInfo
- Publication number
- CA2482896A1 CA2482896A1 CA002482896A CA2482896A CA2482896A1 CA 2482896 A1 CA2482896 A1 CA 2482896A1 CA 002482896 A CA002482896 A CA 002482896A CA 2482896 A CA2482896 A CA 2482896A CA 2482896 A1 CA2482896 A1 CA 2482896A1
- Authority
- CA
- Canada
- Prior art keywords
- ionic liquid
- recited
- product
- polyalphaolefin
- range
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 119
- 239000002608 ionic liquid Substances 0.000 title claims abstract description 104
- 229920013639 polyalphaolefin Polymers 0.000 title claims abstract description 85
- 238000000034 method Methods 0.000 title claims abstract description 65
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 105
- 239000000178 monomer Substances 0.000 claims abstract description 88
- 239000004711 α-olefin Substances 0.000 claims abstract description 39
- 238000006384 oligomerization reaction Methods 0.000 claims abstract description 27
- 239000000203 mixture Substances 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 55
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 239000000539 dimer Substances 0.000 claims description 14
- 229910001507 metal halide Inorganic materials 0.000 claims description 12
- 150000005309 metal halides Chemical class 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 4
- OFHCOWSQAMBJIW-AVJTYSNKSA-N alfacalcidol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C OFHCOWSQAMBJIW-AVJTYSNKSA-N 0.000 claims description 3
- 239000000047 product Substances 0.000 abstract description 94
- 239000007795 chemical reaction product Substances 0.000 abstract description 17
- 239000000314 lubricant Substances 0.000 abstract description 7
- 239000003879 lubricant additive Substances 0.000 abstract description 7
- 238000006116 polymerization reaction Methods 0.000 abstract description 5
- 238000005829 trimerization reaction Methods 0.000 abstract 1
- 239000012071 phase Substances 0.000 description 40
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 28
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 230000000704 physical effect Effects 0.000 description 24
- 238000010924 continuous production Methods 0.000 description 22
- 229940069096 dodecene Drugs 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 238000000926 separation method Methods 0.000 description 9
- 239000013638 trimer Substances 0.000 description 9
- 239000004215 Carbon black (E152) Substances 0.000 description 8
- 230000009849 deactivation Effects 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 8
- 150000002430 hydrocarbons Chemical class 0.000 description 8
- 238000005984 hydrogenation reaction Methods 0.000 description 8
- -1 aluminum halide Chemical class 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 229910052733 gallium Inorganic materials 0.000 description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000013505 freshwater Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- POLXFNKVUMMMHL-UHFFFAOYSA-K n,n-dimethylmethanamine;trichloroalumane;hydrochloride Chemical compound [Al+3].Cl.[Cl-].[Cl-].[Cl-].CN(C)C POLXFNKVUMMMHL-UHFFFAOYSA-K 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000005703 Trimethylamine hydrochloride Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003606 oligomerizing effect Effects 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- SZYJELPVAFJOGJ-UHFFFAOYSA-N trimethylamine hydrochloride Chemical compound Cl.CN(C)C SZYJELPVAFJOGJ-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/14—Catalytic processes with inorganic acids; with salts or anhydrides of acids
- C07C2/20—Acids of halogen; Salts thereof ; Complexes thereof with organic compounds
- C07C2/22—Metal halides; Complexes thereof with organic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/14—Monomers containing five or more carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/125—Compounds comprising a halogen and scandium, yttrium, aluminium, gallium, indium or thallium
- C07C2527/126—Aluminium chloride
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Lubricants (AREA)
Abstract
La présente invention concerne un procédé de production continue d'un produit poly-alpha-oléfinique à haute viscosité en introduisant conjointement un monomère et un catalyseur liquide ionique dans une zone de réaction tout en enlevant en même temps de la zone de réaction un effluent de zone de réaction contenant le poly-alpha-oléfine à haute viscosité. La zone de réaction est utilisée dans des conditions de réaction convenables pour produire le produit poly-alpha-oléfinique à haute viscosité. Le poly-alpha-oléfine à haute viscosité préféré présente une viscosité cinématique dépassant environ 8 cSt et constitue le produit réactionnel issu de la trimérisation, oligomérisation ou polymérisation d'un alpha-oléfine ou d'un mélange d'un ou plusieurs de ses produits. Les poly-alpha-oléfines selon l'invention sont utilisables en tant que lubrifiants or additifs lubrifiants.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US37452802P | 2002-04-22 | 2002-04-22 | |
US60/374528 | 2002-04-22 | ||
PCT/US2003/012821 WO2003089390A2 (fr) | 2002-04-22 | 2003-04-22 | Procede de production de poly-alpha-olefines a haute viscosite en utilisant des catalyseurs liquides ioniques |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2482896A1 true CA2482896A1 (fr) | 2003-10-30 |
Family
ID=29251200
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002482896A Abandoned CA2482896A1 (fr) | 2002-04-22 | 2003-04-22 | Procede de production de poly-alpha-olefines a haute viscosite en utilisant des catalyseurs liquides ioniques |
Country Status (7)
Country | Link |
---|---|
US (2) | US7351780B2 (fr) |
EP (2) | EP1497243A2 (fr) |
JP (1) | JP2005523320A (fr) |
AU (1) | AU2003223727A1 (fr) |
CA (1) | CA2482896A1 (fr) |
RU (1) | RU2004133895A (fr) |
WO (1) | WO2003089390A2 (fr) |
Families Citing this family (35)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7259284B2 (en) * | 2000-05-31 | 2007-08-21 | Chevron Phillips Chemical Company, Lp | Method for manufacturing high viscosity polyalphaolefins using ionic liquid catalysts |
CA2482896A1 (fr) | 2002-04-22 | 2003-10-30 | Chevron Phillips Chemical Company Lp | Procede de production de poly-alpha-olefines a haute viscosite en utilisant des catalyseurs liquides ioniques |
AU2003223729A1 (en) * | 2002-04-22 | 2003-11-03 | Chevron Phillips Chemical Company Lp | Method for manufacturing ionic liquid catalysts |
WO2005042447A1 (fr) * | 2003-10-31 | 2005-05-12 | Chevron Phillips Chemical Company, Lp | Procede et systeme pour le contact entre un catalyseur ionique liquide et de l'oxygene, permettant d'ameliorer une reaction chimique |
CA2543969A1 (fr) * | 2003-10-31 | 2005-05-12 | Chevron Phillips Chemical Company Lp | Procede et systeme permettant d'augmenter le cisaillement afin d'ameliorer une reaction chimique catalysee a liquide ionique |
US7550640B2 (en) * | 2005-01-14 | 2009-06-23 | Exxonmobil Chemical Patents Inc. | High viscosity PAOs based on 1-decene/1-dodecene |
GB0525251D0 (en) | 2005-12-12 | 2006-01-18 | Univ Belfast | Oligomerisation |
US7572943B2 (en) * | 2005-12-20 | 2009-08-11 | Chevron U.S.A. Inc. | Alkylation of oligomers to make superior lubricant or fuel blendstock |
US7572944B2 (en) * | 2005-12-20 | 2009-08-11 | Chevron U.S.A. Inc. | Process for making and composition of superior lubricant or lubricant blendstock |
US7592497B2 (en) * | 2006-03-24 | 2009-09-22 | Exxonmobil Chemical Patents Inc. | Low viscosity polyalphapolefin based on 1-decene and 1-dodecene |
US7544850B2 (en) * | 2006-03-24 | 2009-06-09 | Exxonmobil Chemical Patents Inc. | Low viscosity PAO based on 1-tetradecene |
US7547811B2 (en) * | 2006-03-24 | 2009-06-16 | Exxonmobil Chemical Patents Inc. | High viscosity polyalphaolefins based on 1-hexene, 1-dodecene and 1-tetradecene |
US8143467B2 (en) * | 2007-12-18 | 2012-03-27 | Exxonmobil Research And Engineering Company | Process for synthetic lubricant production |
US8865959B2 (en) * | 2008-03-18 | 2014-10-21 | Exxonmobil Chemical Patents Inc. | Process for synthetic lubricant production |
CA2740217C (fr) * | 2008-10-31 | 2017-03-28 | Chevron Phillips Chemical Company Lp | Systeme et methode de desactivation et d'etanchement d'un catalyseur d'oligomerisation |
US8471085B2 (en) | 2008-10-31 | 2013-06-25 | Chevron Phillips Chemical Company Lp | Oligomerization catalyst system and process for oligomerizing olefins |
EP2418228A4 (fr) * | 2009-04-10 | 2013-09-04 | Idemitsu Kosan Co | Oligomère d'a-oléfine et son procédé de fabrication |
MX362816B (es) * | 2009-06-16 | 2019-02-15 | Chevron Phillips Chemical Co Lp | Oligomerizacion de alfa olefinas usando sistemas de catalizador de metaloceno-ssa y uso de las polialfaolefinas resultantes para preparar mezclas lubricantes. |
US8604258B2 (en) | 2009-08-10 | 2013-12-10 | Chevron U.S.A. Inc. | Base oil having high kinematic viscosity and low pour point |
US8124821B2 (en) | 2009-08-10 | 2012-02-28 | Chevron U.S.A. Inc. | Oligomerization of propylene to produce base oil products using ionic liquids-based catalysis |
US8101809B2 (en) * | 2009-08-10 | 2012-01-24 | Chevron U.S.A. Inc. | Base oil composition comprising oligomerized olefins |
US9267091B2 (en) | 2009-08-10 | 2016-02-23 | Chevron U.S.A. Inc. | Tuning an oligomerizing step that uses an acidic ionic liquid catalyst to produce a base oil with selected properties |
US8487154B2 (en) * | 2010-03-17 | 2013-07-16 | Chevron U.S.A. Inc. | Market driven alkylation or oligomerization process |
US8895794B2 (en) * | 2010-03-17 | 2014-11-25 | Chevron U.S.A. Inc. | Process for producing high quality gasoline blending components in two modes |
US8455708B2 (en) | 2010-03-17 | 2013-06-04 | Chevron U.S.A. Inc. | Flexible production of alkylate gasoline and distillate |
US8471086B2 (en) * | 2010-06-28 | 2013-06-25 | Chevron U.S.A. Inc. | Process to control product selectivity |
EP2593224A4 (fr) | 2010-07-07 | 2014-01-29 | Conocophillips Co | Supports hétérogènes pour catalyseurs homogènes |
US8524968B2 (en) | 2010-12-13 | 2013-09-03 | Chevron U.S.A. Inc. | Process to make base oil by oligomerizing low boiling olefins |
US8222471B2 (en) * | 2010-12-13 | 2012-07-17 | Chevron U.S.A. Inc. | Process for making a high viscosity base oil with an improved viscosity index |
CN102776023B (zh) * | 2011-05-11 | 2015-02-25 | 中国石油化工股份有限公司 | 一种高粘度聚α-烯烃合成油及其制备方法 |
US9669377B2 (en) * | 2014-12-12 | 2017-06-06 | Uop Llc | Ionic liquid reactor with heat exchanger |
WO2016161203A1 (fr) * | 2015-03-31 | 2016-10-06 | Uop Llc | Procédés d'oligomérisation d'oléfines faisant appel à des microémulsions de liquide ionique de type halogénométallate |
WO2016161200A1 (fr) | 2015-03-31 | 2016-10-06 | Uop Llc | Micro-émulsions de liquide ionique halométallate |
US10435491B2 (en) | 2015-08-19 | 2019-10-08 | Chevron Phillips Chemical Company Lp | Method for making polyalphaolefins using ionic liquid catalyzed oligomerization of olefins |
EP3896141B1 (fr) * | 2020-04-14 | 2023-08-30 | Indian Oil Corporation Limited | Procédé de contrôle de la viscosité cinématique d'une polyalphaoléfine |
Family Cites Families (39)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2405950A (en) * | 1943-03-27 | 1946-08-20 | Du Pont | Process for polymerizing olefins |
US3647912A (en) * | 1969-03-04 | 1972-03-07 | Exxon Research Engineering Co | Preparation of linear olefin products |
CA1208196A (fr) | 1982-03-10 | 1986-07-22 | Raymond F. Watts | Produit lubrifiant |
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-
2003
- 2003-04-22 CA CA002482896A patent/CA2482896A1/fr not_active Abandoned
- 2003-04-22 US US10/420,261 patent/US7351780B2/en not_active Expired - Fee Related
- 2003-04-22 JP JP2003586112A patent/JP2005523320A/ja not_active Abandoned
- 2003-04-22 RU RU2004133895/04A patent/RU2004133895A/ru not_active Application Discontinuation
- 2003-04-22 AU AU2003223727A patent/AU2003223727A1/en not_active Abandoned
- 2003-04-22 WO PCT/US2003/012821 patent/WO2003089390A2/fr active Application Filing
- 2003-04-22 EP EP03719928A patent/EP1497243A2/fr not_active Withdrawn
- 2003-04-22 EP EP10176993A patent/EP2272814A2/fr not_active Withdrawn
-
2008
- 2008-03-14 US US12/048,368 patent/US7615598B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
AU2003223727A1 (en) | 2003-11-03 |
US20040030075A1 (en) | 2004-02-12 |
US7351780B2 (en) | 2008-04-01 |
WO2003089390A3 (fr) | 2004-03-18 |
EP1497243A2 (fr) | 2005-01-19 |
US20080161623A1 (en) | 2008-07-03 |
EP2272814A2 (fr) | 2011-01-12 |
RU2004133895A (ru) | 2005-06-10 |
WO2003089390A2 (fr) | 2003-10-30 |
US7615598B2 (en) | 2009-11-10 |
JP2005523320A (ja) | 2005-08-04 |
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